Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

28. Carbohydrates

Monosaccharides - Acylation

Organic Chemistry

28. Carbohydrates

Monosaccharides - Acylation

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2:47 minutes

Problem 32a

Textbook Question

Suggest a synthesis of the following acylated sugars.
(a)

Verified step by step guidance

Identify the sugar backbone: The central structure is a pyranose ring, which is a six-membered ring typically found in sugars. The presence of multiple ester groups indicates that this is an acylated sugar.

Determine the acyl groups: The acyl groups attached to the sugar are phenyl esters (PhCOO-) and an isopropyl ester (CH3CH(CH3)COO-). These groups are attached to the hydroxyl groups of the sugar.

Select the starting sugar: Begin with a simple sugar that has the same pyranose ring structure, such as glucose or galactose, which can be acylated at the hydroxyl groups.

Perform acylation: Use acyl chlorides or anhydrides corresponding to the acyl groups identified (benzoyl chloride for PhCOO- and isobutyryl chloride for CH3CH(CH3)COO-) in the presence of a base like pyridine to acylate the hydroxyl groups of the sugar.

Purify the product: After the acylation reaction, purify the acylated sugar using techniques such as recrystallization or chromatography to obtain the desired acylated sugar structure.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acylation

Acylation is a chemical reaction that introduces an acyl group into a molecule. In organic chemistry, this process often modifies the properties of sugars, enhancing their reactivity or solubility. Understanding the types of acyl groups and their effects on the sugar structure is crucial for synthesizing acylated sugars.

Synthesis of Sugars

The synthesis of sugars involves various chemical reactions to construct or modify carbohydrate structures. This includes the use of protecting groups, coupling reactions, and specific reagents that facilitate the formation of glycosidic bonds. A solid grasp of carbohydrate chemistry is essential for designing effective synthetic pathways.

Reaction Mechanisms

Understanding reaction mechanisms is vital for predicting the outcomes of chemical reactions, including those involving acylated sugars. Mechanisms describe the step-by-step process of how reactants transform into products, including intermediates and transition states. Familiarity with these concepts allows chemists to optimize conditions for desired reactions.

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